Реакция #888

Уравнение реакции

1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

KBr

→

2,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan

Растворители

phosphorus trichloride

Условия реакции

Обработка

1. 1
   Температураunder reflux for 3-4 hr (TLC followed)
2. 2
   ДругоеThe excess PCl3 was removed by distillation
3. 3
   Другоеthe residue was triturated with ice/water (exothermic reaction)
4. 4
   ЭкстракцияThe solution was extracted with dichloromethane (75 ml)
5. 5
   Промывкаthe dichloromethane layer was washed with saturated sodium bicarbonate solution, water
6. 6
   Другоеdried (Na2 SO4)
7. 7
   ДругоеThe solvent was removed under reduced pressure
8. 8
   ДругоеThe residual solid was chromatographed over silica gel
9. 9
   ДругоеAn off white crystalline solid was obtained

Методика

A solution of 5.0 g (0.01 mole) 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene in 10 ml phosphorus trichloride was heated under reflux for 3-4 hr (TLC followed). The excess PCl3 was removed by distillation and the residue was triturated with ice/water (exothermic reaction). The solution was extracted with dichloromethane (75 ml) and the dichloromethane layer was washed with saturated sodium bicarbonate solution, water, and dried (Na2 SO4). The solvent was removed under reduced pressure. The residual solid was chromatographed over silica gel using ether:hexane (2:8 to 1:1) as eluant. An off white crystalline solid was obtained, 2.78 g (56%), mp 92°-3° C. IR (KBr) 2923, 2851, 1560, 1506, 1467, 1390, 1209, 1072, 1066, 945, 825, 707, 486. 1H NMR (CDCl3 /35° C.) 7.69 (d, 2H, J=8.8), 7.46-7.43 (m, 6H), 7.12 (d, 2H, J=8.3), 7.0 (d, 2H, J=8.3), 6.47 (s, 1H), 2.31 (s, 3H). 13C NMR (CDCl3 /135° C.) 150.8, 150.1, 142.8, 139.3, 133.0, 131.9, 131.7, 130.3, 129.1, 128.6, 125.1, 125.0, 121.8, 120.5, 117.1, 102.7, 20.6. MS m/e 484 (M+).

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